Compound for organic electric element, organic electric element using same, and electronic apparatus thereof

ABSTRACT

Provided are a compound capable of lowering a driving voltage, enhancing light emitting efficiency and thermal resistance, and improving lifespan and color purity of the element, an organic element using the same, and an electric device for the same.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority from and the benefit under 35 U.S.C. §119(a) of Korean Patent Application No. 10-2015-0090751 filed on Jun.25, 2015, the contents of which are hereby incorporated by reference forall purposes as if fully set forth herein.

BACKGROUND Technical Field

The present invention relates to compounds for organic electricelements, organic electric elements using the same, and electronicdevices thereof.

Background Art

Flat panel display devices are playing a very important role insupporting a high image information society, showing rapid growth mainlyin the Internet in recent years.

In particular, an organic electroluminescent device (organic EL device)capable of being driven at low voltage as self-luminous type hasexcellent viewing angle and contrast ratio, is lightweight and thinbecause no backlight is required, and has advantages in terms of powerconsumption, compared with liquid crystal displays (LCDs) which are themainstream of flat panel display devices. Also, organic EL device isalso getting attention as next generation display device because oftheir high response speed and wide color reproduction range.

Generally, an organic electroluminescent device is formed on a glasssubstrate in the following order: an anode made of a transparentelectrode, an organic thin film including a light emitting region, and ametal electrode. Here, the organic thin film may include a holeinjection layer (HIL), a hole transport layer (HTL), an electrontransport layer (ETL), or an electron injection layer (EIL) in additionto an emitting layer (EML) and may further include a anemission-auxiliary layer, an electron blocking layer (EBL) or a holeblocking layer (HBL) on the emission characteristics of the lightemitting layer.

When an electric field is applied to the organic electroluminescentdevice having such a structure, holes are injected from the anode andelectrons are injected from the cathode. The injected holes andelectrons recombine in the light emitting layer through the holetransporting layer and the electron transporting layer, respectively,thereby forming luminescent excitons. The formed luminescent excitonsemit light while transitioning to the ground states. At this time, aluminescent dye (guest) is doped in the light emitting layer (host) toincrease the efficiency and stability of the luminescent state.

In order to utilize the organic electroluminescent device in variousdisplay media, the lifetime of the device is important, and variousstudies are currently under way to increase the lifetime of the organicelectroluminescent device.

Particularly, various studies for an excellent lifetime characteristicof an organic electric device have been conducted on an organic materialwhich is inserted into a buffer layer such as a hole transporting layeror an emission-auxiliary layer. For this purpose, a hole injecting layerand a hole transporting layer material having high uniformity and lowcrystallinity are required for forming a thin film after deposition,while giving high hole transporting characteristics from the anode tothe organic layer.

In addition, it is required to develop material of a hole injectionlayer and a hole transport layer that retards penetration/diffusion ofmetal oxides from an anode electrode (ITO) into an organic layer, whichis one cause for the shortened life span of an organic electric element,and has stability against Joule heat generated during the operation ofan organic electric element, that is, a high glass transitiontemperature. Also, it has been reported that a low glass transitiontemperature of a hole transport layer material has a great effect on thelife span of an organic electric element because the uniformity of athin film surface collapses during the operation of the element.

In general, deposition is a main method of forming an OLED, and thusthere is an actual need to develop a material that is durable to such adeposition method, that is, a highly heat-resistant material.

Currently, the major overcoming problem of organic light emittingdevices is that the problem of power consumption and lifetime must besolved as the panel size of a mobile phone or a tablet PC becomeslarger. However, it is difficult to simultaneously overcome the drivingvoltage and the lifetime solely by the hole transporting layer material.

This is because most of the materials having excellent hole transportingability, that is, materials having high hole mobility, mostly have aplanar structure (e.g., naphthyl, fluorene, phenanthrene), and the holemobility and life time are increased when compounds having the abovestructure (with planarity) up to a certain number are introduced as asubstituent of a hole transporting material, however, if the moleculesare introduced excessively in order to lower a driving voltage requiredin the present industry, it is possible to drive at low voltage as thedriving voltage is going down but the characteristics of lifetime areremarkably deteriorated.

In the case of a molecule in which planar structures are excessivelyintroduced, holes are trapped and stabilized between the platestructures when the constant current is continuously supplied in theevaluation of device lifetime, so that the hole mobility is lowered, asa result, the driving voltage rises in order to apply a constantcurrent, resulting in an adverse effect on the lifetime of the device.This is expressed by the following equation.

$\begin{matrix}{J = {{\frac{9}{8}{\epsilon\mu}\frac{V^{2}}{d^{3}}\theta} = {\frac{9}{8}{\epsilon\mu}\frac{1}{d}F^{2}\theta}}} & \left\langle {{Equation}\mspace{14mu} 1} \right\rangle\end{matrix}$

J=Space Charge limited current, ε=Permittibility

μ=Mobility Coefficient, θ=Charge Trap Coefficient (Free Carrier/totalCarrier)

V=Voltage, d=Thickness

When the number of free carriers decreases due to a trap phenomenon, ina current driven organic electroluminescent device requiring a constantcurrent, the value of θ decreases and the driving voltage rises. Thismay bring about a very fatal effect on the lifetime.

Therefore, as described above, introduction of a certain number or moreof the plate structure capable of increasing the hole mobility cause aharmful effect on the lifetime, and thus, there is a limit to loweringthe driving voltage by using it.

On the other hand, it can be seen that the compound substituted withdeuterium shows much thermodynamic behavior as compared with thenon-substituted compound. As an example of such thermodynamicproperties, comparing the iridium compound substituted with deuteriumwith the non-substituted compound, the characteristics are different dueto the difference between the bond length of carbon and hydrogen and thebond length of carbon and deuterium. It can be confirmed that the vander Waals force between molecules of the compound substituted withdeuterium due to the short bonding length becomes weaker comparing tothe non-substituted compound, and thus it shows higher luminousefficiency.

When the compound is substituted with deuterium, the energy of the zeropoint energy, that is, the bottom state is lowered and the molecularhardcore volume becomes smaller as the bond length of carbon anddeuterium becomes shorter than the bond length of carbon and hydrogen.Thus, the electron polarizability can be reduced, and the thin filmvolume can be increased by weakening the intermolecular interaction (J.Polym. Sci. 1980, 18, 853). It is considered that these characteristicscan produce an effect of lowering the crystallinity of the thin film,that is, an amorphous state and, in general, it is very effective torealize the necessary amorphous state in order to improve lifetime anddriving characteristics of an organic electroluminescent device (Chem.Rev. 2007, 107, 953).

However, many studies have not been conducted on a hole transportingmaterial which can lower the driving voltage and improve the holetransfer ability by substituting with deuterium, and accordingly, it isstrongly required to develop materials of the emission-auxiliary layerand the hole transport layer.

SUMMARY

In order to solve one or more of the above-mentioned problems in priorart, an aspect of the present invention is to provide a compound havingefficient electron blocking ability and hole transport ability by usingthe compound substituted with deuterium, and allowing to lower a drivingvoltage, to improve luminous efficiency, to have a high heat-resistance,and to improve color purity and lifetime of the element, an organicelectric element comprising the same, and an electronic device thereof.

In accordance with an aspect of the present invention, the compoundrepresented by the following formula is provided. The following formularepresents a compound in which amine group is bonded to a dibenzofurancore through a linking group (comprising a single bond), wherein atleast one of L¹, L², Ar¹ and Ar² is a C₆˜C₆₀ aryl group substituted withone or more deuterium.

In another aspect of the present invention, organic electric elementscomprising the compound represented by the formula 1 above andelectronic devices including the organic electric element are provided.

According to the present invention, a specific compound in which adibenzofuran core and an arylamine group substituted with deuterium arebonded to each other through a linking group is used as a material forthe organic electric device, thereby lowering the driving voltage andimproving the hole transporting ability and thermal stability. As aresult, luminous efficiency, heat-resistance, and lifetime of theorganic electric elements can be improved

BRIEF DESCRIPTION OF THE DRAWINGS

The FIGURE illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine, bromine, chlorine or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has a single bond of 1 to 60 carbon atoms, and means a radical ofa saturated aliphatic functional group including a linear alkyl group, abranched chain alkyl group, a cycloalkyl group (alicyclic), a cycloalkylgroup substituted with an alkyl group, an alkyl group substituted with acycloalkyl group and the like.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl” as usedherein includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “heteroalkyl” as used herein meansalkyl substituted one or more carbon atoms constituting an alkyl groupwith heteroatom.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms,and includes a linear alkyl group, or a branched chain alkyl group.

Unless otherwise stated, the term “cycloalkyl” as used herein means, butnot limited to, alkyl forming a ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group” as used herein means an alkyl group to which an oxygenradical is attached, but not limited to, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenoxyl group”, “alkenoxy group”,“alkenyloxy group” or “alkenyloxy group” as used herein means an alkenylgroup to which an oxygen radical is attached, but not limited to, andhas 2 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group” asused herein means an aryl group to which an oxygen radical is attached,but not limited to, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms. Herein, thearyl group or arylene group means a monocyclic or polycyclic aromaticgroup, and may also be formed in conjunction with an adjacent group. Forexample, aryl group may be a phenyl group, a biphenyl group, a fluorenegroup, spirofluorene group or a spirobifluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substitutes with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heteroalkyl” as used herein meansalkyl containing one or more heteroatoms. Unless otherwise stated, theterm “heteroaryl group” or “heteroarylene group” as used herein means,but not limited to, a C₂ to C₆₀ aryl or arylene group containing one ormore heteroatoms, but not limited to, includes at least one ofmonocyclic and polycyclic rings, and may also be formed in conjunctionwith an adjacent group.

Unless otherwise stated, the term “heterocyclic group” as used hereincontains one or more heteroatoms, but not limited to, has 2 to 60 carbonatoms, includes at least one of monocyclic and polycyclic rings, and mayinclude hetero-alicyclic and/or aromatic group containing. Also, theheterocyclic group may also be formed in conjunction with an adjacentgroup.

Unless otherwise stated, the term “heteroatom” as used herein representsat least one of N, O, S, P, and Si.

Also, the term “heterocyclic group” may include SO₂ instead of carbonconsisting of cycle. For example, “heterocyclic group” includes compoundbelow.

Unless otherwise stated, the term “aliphatic” as used herein means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring” as used herein means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring” means an aliphatic ring having3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, ahetero ring having 2 to 60 carbon atoms, or a fused ring formed by thecombination of them, and includes a saturated or unsaturated ring.

Hetero compounds or hetero radicals other than the above-mentionedhetero compounds each contain, but not limited to, one or moreheteroatoms.

Unless otherwise stated, the term “carbonyl” as used herein isrepresented by —COR′, wherein R′ may be hydrogen, an alkyl having 1 to20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkylhaving 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, analkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “ether” as used herein is representedby —R—O—R′, wherein R′ may be hydrogen, an alkyl having 1 to 20 carbonatoms, an aryl having 6 to 30 carbon atoms, a cycloalkyl having 3 to 30carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynl having 2to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylamine group, aC₁-C₂₀ alkylthio group, a C₆-C₂₀ arylthio group, a C₂-C₂₀ alkenyl group,a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₆₀ aryl group,a C₆-C₂₀ aryl group substituted by deuterium, a C₈-C₂₀ arylalkenylgroup, a silane group, a boron group, a germanium group, and a C₂-C₂₀heterocyclic group.

Otherwise specified, the Formulas used in the present invention are asdefined in the index definition of the substituent of the followingFormula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole R¹ is linked to any one of thecarbon atoms constituting the benzene ring, when a is an integer of 2 or3, the substituent R¹s may be the same and different, and are linked tothe benzene ring as follows. When a is an integer of 4 to 6, thesubstituents R¹s may be the same and different, and are linked to thebenzene ring in a similar manner to that when a is an integer of 2 or 3,hydrogen atoms linked to carbon constituents of the benzene ring beingnot represented as usual.

FIGURE illustrates an organic electric element according to anembodiment of the present invention.

Referring to FIGURE, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer between the first electrode 110 and the second electrode180, which contains the inventive compound. Here, the first electrode120 may be an anode (positive electrode), and the second electrode 180may be a cathode (negative electrode). In the case of an invertedorganic electric element, the first electrode may be a cathode, and thesecond electrode may be an anode.

The organic material layer may include a hole injection layer 130, ahole transport layer 140, a light emitting layer 150, an electrontransport layer 160, and an electron injection layer 170 formed on thefirst electrode 120. Here, layers other than a light emitting layer 150may be omitted. The organic material layer may further include a holeblocking layer, an electron blocking layer, an emission-auxiliary layer151, a buffer layer 141, etc., and the electron transport layer 160 orthe like may serve as the hole blocking layer.

Although not shown, the organic electric element according to anembodiment of the present invention may further include at least oneprotective layer or one capping layer formed on at least one of thesides the first and second electrodes, which is a side opposite to theorganic material layer.

The inventive compound employed in the organic material layer may beused as a material of a hole injection layer 130, a hole transport layer140, an electron transport layer 160, an electron injection layer 170,as a host or a dopant material of a light emitting layer 150, or as amaterial of a capping layer. Preferably, the inventive compound may beused as a hole transport layer 140 and/or the emission-auxiliary layer151. Also, the inventive compound employed in the organic material layermay be used as a single compound or as a mixture of two or more kinds.

On the other hand, even if the core is the same, the band gap, theelectrical characteristics, the interface characteristics, and the likemay be different depending on which substituent is bonded at whichposition. Therefore, the selection of core and the combination ofsub-substituents coupled thereto are also very important. Specially,long life span and high efficiency can be simultaneously achieved whenthe optimal combination of energy levels and T1 values, inherentmaterial properties (mobility, interfacial properties, etc.), and thelike among the respective layers of an organic material layer isachieved.

As already described above, generally, in order to solve the emissionproblem with a hole transport layer of an organic electric element, itis preferable that an emission-auxiliary layer is formed between thehole transport layer and a light emitting layer, and it is necessary todevelop different emission-auxiliary layers according to respectivelight emitting layers (R, G, B). On the other hand, it is very difficultto infer the characteristics of an emission-auxiliary layer, even if thecore of an emission-auxiliary layer is similar, because it is necessaryto grasp the correlation between the emission-auxiliary layer and a holetransport layer and a light emitting layer (host).

Therefore, according to the present invention, energy levels betweenorganic material layers and T₁ values, inherent material properties(mobility, interfacial properties, etc.), and the like can be optimizedby forming a hole transport layer or an emission-auxiliary layer whichcomprise the compound represented by the Formula 1, and thus it ispossible to simultaneously improve the life span and efficiency of theorganic electronic element.

The organic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method. For example, the organic electric element may be manufactured bydepositing a metal, a conductive metal oxide, or a mixture thereof onthe substrate to form the anode 120, forming the organic material layerincluding the hole injection layer 130, the hole transport layer 140,the light emitting layer 150, the electron transport layer 160, and theelectron injection layer 170 thereon, and then depositing a material,which can be used as the cathode 180, thereon.

Also, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, nozzle printing, inkjet printing, slot coating, dip coating,roll-to-roll, doctor blading, screen printing, or thermal transfer,instead of deposition. Since the organic material layer according to thepresent invention may be formed in various ways, the scope of protectionof the present invention is not limited by a method of forming theorganic material layer.

The organic electric element according to an embodiment of the presentinvention may be of a top emission type, a bottom emission type, or adual emission type depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of highresolution realization, an excellent processability, and being producedby using conventional color filter technologies for LCDs. Variousstructures for WOLED which mainly used as back light units have beensuggested and patented. WOLED may employ various arrangement methods,representatively, a parallel side-by-side arrangement method of R(Red),G(Green), B(Blue) light-emitting units, a vertical stack arrangementmethod of RGB light-emitting units, and a CCM (color conversionmaterial) method in which electroluminescence from a blue (B) organiclight emitting layer, and the present invention may be applied to suchWOLED.

Also, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode, anorganic solar cell, an organic photo conductor, an organic transistor,and an element for monochromatic or white illumination.

Another embodiment of the present invention provides an electronicdevice including a display device which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, the compound according to an aspect of the presentinvention will be described.

The compound according to an aspect of the present invention isrepresented by the following Formula 1.

wherein,

R¹ and R² are each independently selected from the group consisting ofdeuterium, tritium, halogen, a cyano group, a nitro group, a C₆-C₆₀ arylgroup, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxyl group, and a C₆-C₃₀ aryloxyl group, theymay be each optionally further substituted with one or more substituentsselected from the group consisting of deuterium, halogen, a silane groupsubstituted or unsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ arylgroup, a siloxane group, a boron group, a germanium group, a cyanogroup, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group,a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, afluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, aC₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀arylalkenyl group,

m is an integer of 0 to 4, and when m is an integer of 2 or more, R¹smay be each the same or different from each other,

n is an integer of 0 to 3, and when n is an integer of 2 or more, R²smay be each the same or different from each other.

Ar¹ and Ar² are each independently a C₆-C₆₀ aryl group, they may be eachoptionally further substituted with one or more substituents selectedfrom the group consisting of deuterium, halogen, a silane groupsubstituted or unsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ arylgroup, a siloxane group, a boron group, a germanium group, a cyanogroup, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group,a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, afluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, aC₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀arylalkenyl group,

with the proviso that at least one of L¹, L², Ar¹ and Ar² may be aC₆-C₆₀ aryl group substituted with one or more deuterium.

L¹ is selected from the group consisting of a single bond; a C₆-C₆₀arylene group; a divalent C₂-C₆₀ heterocyclic group containing at leastone heteroatom selected from the group consisting of O, N, S, Si, and P;a fluorenylene group; a divalent fused ring formed by a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; and a divalent C₁-C₆₀ aliphatichydrocarbon group, and they (except for a single bond) may be eachoptionally further substituted with one or more substituents selectedfrom the group consisting of deuterium, halogen, a silane groupsubstituted or unsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ arylgroup, a siloxane group, a boron group, a germanium group, a cyanogroup, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group,a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, afluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, aC₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀arylalkenyl group,

L² and L³ are each independently selected from the group consisting of asingle bond; and a C₆-C₆₀ arylene group, and they (except for a singlebond) may be each optionally further substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group substituted or unsubstituted with a C₁-C₂₀ alkyl group or aC₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, acyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxylgroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted withdeuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀arylalkenyl group,

with the proviso that when both L² and L³ are C₆ arylene group, the casewhere Ar¹ is a C₆ aryl group substituted with deuterium and Ar² is a C₆aryl group substituted with deuterium is excluded.

Here, at least one of Ar¹ and Ar² may be represented by Formula 1abelow.

Wherein, R³ may be selected from the group consisting of deuterium,halogen, a silane group substituted or unsubstituted with a C₁-C₂₀ alkylgroup or a C₆-C₂₀ aryl group, a siloxane group, a boron group, agermanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group,a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl groupsubstituted with deuterium, a fluorenyl group, a C₃-C₂₀ cycloalkylgroup, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenyl group, and atleast one of R³ may be deuterium.

o is an integer of 0 to 7, and, and R³s are each the same or differentfrom each other when o is an integer of 2 or more, and at least one ofR³ is deuterium or a C₆-C₂₀ aryl group substituted with deuterium when ois an integer of 1 to 7.

Here, Formula 1 above may be represented by any one of Formulas 2 to 5below.

In Formulas 2 to 5, R¹, R², L¹ to L³, Ar¹, Ar², m and n are the same asdefined in Formula 1 above.

Specifically, the compound represented by Formula 1 may be any one ofthe following compounds P-1 to P-60.

Hereinafter, synthesis examples of the compound represented by Formula 1according to one embodiment of the present invention and preparationexamples of an organic electric element will be described in detail byway of examples. However, these synthesis or preparation examples areonly illustrative for those skilled in the art to easily practice thepresent invention. The scope of the present invention is not limited tothese synthesis or preparation examples.

EXAMPLES Synthesis Example

The compound (final products) represented by Formula 1 according to thepresent invention are synthesized by reacting Sub 1 and Sub 2 as shownin Reaction Scheme 1, but are not limited thereto.

I. Synthesis of Sub 1

Sub 1 of the Reaction Scheme 1 can be synthesized according to, but notlimited to, the reaction route of the following Reaction Scheme 2.

Here, Hal¹ may be Br or I.

Synthesis Examples of compounds comprised in Sub 1 are as follows.

1. Synthesis Example of Sub 1-3

(1) Synthesis of Sub 1-I-3

The starting material 3-bromo-[1,1′-biphenyl]-2-ol (59.89 g, 240.43mmol) was placed in a round bottom flask together with Pd(OAc)₂ (5.40 g,24.04 mmol), 3-nitropyridine (2.98 g, 24.04 mmol), and dissolved in C₆F₆(360 ml) and DMI (240 ml). Then, tert-butyl peroxybenzoate (93.40 g,480.85 mmol) was added and the stirring at 90° C. was followed. When thereaction was completed, the reaction product was extracted with CH₂Cl₂and water, and then, the organic layer was dried with MgSO₄ andconcentrated. Then, the concentrate was passed through silica gel columnand recrystallized to obtain 29.11 g (yield: 49%) of the product.

(2) Synthesis of Sub 1-II-3

Sub 1-I-3 (29.11 g, 117.81 mmol) obtained in the above synthesis wasdissolved in DMF (590 ml) in a round bottom flask, and then,Bis(pinacolato)diboron (32.91 g, 129.59 mmol), Pd(dppf)Cl₂ (2.89 g, 3.53mmol), KOAc (34.69 g, 353.43 mmol) were added and stirred at 90° C. Whenthe reaction was completed, DMF was removed by distillation andextracting with CH₂Cl₂ and water was followed. Then, the organic layerwas dried with MgSO₄ and concentrated and the concentrate was passedthrough silica gel column and recrystallized to obtain 28.42 g (yield:82%) of the product.

(3) Synthesis of Sub 1-3

Sub 1-II-3 (14.21 g, 48.31 mmol) obtained in the above synthesis wasdissolved in THF (170 ml) in a round bottom flask, and then,1,4-dibromobenzene (12.54 g, 53.14 mmol), Pd(PPh₃)₄ (1.67 g, 1.45 mmol),NaOH (5.80 g, 144.93 mmol), water (85 ml) were added and stirred at 80°C. When the reaction was completed, the reaction product was extractedwith CH₂Cl₂ and water, and then, the organic layer was dried with MgSO₄and concentrated. Then, the concentrate was passed through silica gelcolumn and recrystallized to obtain 12.49 g (yield: 80%) of the product.

2. Synthesis Example of Sub 1-6

(1) Synthesis of Sub 1-I-6

Pd(OAc)₂ (3.60 g, 16.03 mmol), 3-nitropyridine (1.99 g, 16.03 mmol),tert-butyl peroxybenzoate (62.28 g, 320.65 mmol), C₆F₆ (240 ml), DMI(160 ml) were added to the starting material6-(benzo[b]thiophen-2-yl)-3-bromo-[1,1′-biphenyl]-2-ol (61.13 g, 160.32mmol), and then 24.32 g (yield: 40%) of the product was obtained byusing the same manner as described above for the synthesis of Sub 1-I-3.

(2) Synthesis of Sub 1-II-6

Bis(pinacolato)diboron (17.91 g, 70.54 mmol), Pd(dppf)Cl₂ (1.57 g, 1.92mmol), KOAc (18.88 g, 192.37 mmol), DMF (320 ml) were added to Sub 1-I-6(24.32 g, 64.12 mmol) obtained in the above synthesis, and then 21.05 g(yield: 77%) of the product was obtained by using the same manner asdescribed above for the synthesis of Sub 1-II-3.

(3) Synthesis of Sub 1-6

1,4-dibromobenzene-d4 (13.03 g, 54.31 mmol), Pd(PPh₃)₄ (1.71 g, 1.48mmol), NaOH (5.92 g, 148.12 mmol), THF (170 ml), water (85 ml) wereadded to Sub 1-II-6 (21.05 g, 49.37 mmol) obtained in the abovesynthesis, and then 14.06 g (yield: 62%) of the product was obtained byusing the same manner as described above for the synthesis of Sub 1-3.

3. Synthesis Example of Sub 1-10

2,7-dibromo-9,9-dimethyl-9H-fluorene (17.73 g, 50.37 mmol), Pd(PPh₃)₄(1.59 g, 1.37 mmol), NaOH (5.50 g, 137.38 mmol), THF (160 ml), water (80ml) were added to Sub 1-II-3 (13.47 g, 45.79 mmol) obtained in the abovesynthesis, and then 14.69 g (yield: 73%) of the product was obtained byusing the same manner as described above for the synthesis of Sub 1-3.

4. Synthesis Example of Sub 1-22

(1) Synthesis of Sub 1-I-22

Pd(OAc)₂ (5.84 g, 26.02 mmol), 3-nitropyridine (3.23 g, 26.02 mmol),tert-butyl peroxybenzoate (101.07 g, 520.35 mmol), C₆F₆ (390 ml), DMI(260 ml) were added to the starting material4′-bromo-[1,1′-biphenyl]-2-ol (64.81 g, 260.18 mmol), and then 30.21 g(yield: 47%) of the product was obtained by using the same manner asdescribed above for the synthesis of Sub 1-I-3.

(2) Synthesis of Sub 1-II-22

Bis(pinacolato)diboron (34.15 g, 134.49 mmol), Pd(dppf)Cl₂ (3.00 g, 3.67mmol), KOAc (36.00 g, 366.79 mmol), DMF (610 ml) were added to Sub1-I-22 (30.21 g, 122.26 mmol) obtained in the above synthesis, and then30.57 g (yield: 85%) of the product was obtained by using the samemanner as described above for the synthesis of Sub 1-II-3.

(3) Synthesis of Sub 1-22

1,3-dibromobenzene (11.09 g, 47.01 mmol), Pd(PPh₃)₄ (1.48 g, 1.28 mmol),NaOH (5.13 g, 128.20 mmol), THF (150 ml), water (75 ml) were added toSub 1-II-22 (12.57 g, 42.73 mmol) obtained in the above synthesis, andthen 10.77 g (yield: 78%) of the product was obtained by using the samemanner as described above for the synthesis of Sub 1-3.

5. Synthesis Example of Sub 1-24

2-bromo-4-iododibenzo[b,d]thiophene (22.00 g, 56.54 mmol), Pd(PPh3)4(1.78 g, 1.54 mmol), NaOH (6.17 g, 154.21 mmol), THF (180 ml), water (90ml) were added to Sub 1-II-22 (15.12 g, 51.40 mmol) obtained in theabove synthesis, and then 15.45 g (yield: 70%) of the product wasobtained by using the same manner as described above for the synthesisof Sub 1-3.

6. Synthesis Example of Sub 1-26

Pd(OAc)₂ (6.75 g, 30.04 mmol), 3-nitropyridine (3.73 g, 30.04 mmol),tert-butyl peroxybenzoate (116.71 g, 600.88 mmol), C₆F₆ (450 ml), DMI(300 ml) were added to the starting material5-bromo-[1,1′-biphenyl]-2-ol (74.84 g, 300.44 mmol), and then 37.86 g(yield: 51%) of the product was obtained by using the same manner asdescribed above for the synthesis of Sub 1-I-3.

7. Synthesis Example of Sub 1-27

(1) Synthesis of Sub 1-II-27

Bis(pinacolato)diboron (31.29 g, 123.23 mmol), Pd(dppf)Cl₂ (2.74 g, 3.36mmol), KOAc (32.98 g, 336.07 mmol), DMF (560 ml) were added to Sub 1-26(27.68 g, 112.02 mmol) obtained in the above synthesis, and then 28.34 g(yield: 86%) of the product was obtained by using the same manner asdescribed above for the synthesis of Sub 1-II-3.

(2) Synthesis of Sub 1-27

1,4-dibromobenzene (11.93 g, 50.56 mmol), Pd(PPh₃)₄ (1.59 g, 1.38 mmol),NaOH (5.52 g, 137.89 mmol), THF (160 ml), water (80 ml) were added toSub 1-II-27 (13.52 g, 45.96 mmol) obtained in the above synthesis, andthen 12.33 g (yield: 83%) of the product was obtained by using the samemanner as described above for the synthesis of Sub 1-3.

8. Synthesis Example of Sub 1-31

4,4′-dibromo-1,1′-biphenyl (14.76 g, 47.31 mmol), Pd(PPh₃)₄ (1.49 g,1.29 mmol), NaOH (5.16 g, 129.02 mmol), THF (150 ml), water (75 ml) wereadded to Sub 1-II-27 (12.65 g, 43.01 mmol) obtained in the abovesynthesis, and then 13.57 g (yield: 79%) of the product was obtained byusing the same manner as described above for the synthesis of Sub 1-3.

9. Synthesis Example of Sub 1-49

(1) Synthesis of Sub 1-I-49

Pd(OAc)₂ (3.59 g, 15.99 mmol), 3-nitropyridine (1.98 g, 15.99 mmol),tert-butyl peroxybenzoate (62.10 g, 319.74 mmol), C₆F₆ (240 ml), DMI(160 ml) were added to the starting material6′-bromo-[1,1′:3′,1″-terphenyl]-2-ol (51.99 g, 159.87 mmol), and then23.25 g (yield: 45%) of the product was obtained by using the samemanner as described above for the synthesis of Sub 1-I-3.

(2) Synthesis of Sub 1-II-49

Bis(pinacolato)diboron (20.10 g, 79.14 mmol), Pd(dppf)Cl₂ (1.76 g, 2.16mmol), KOAc (21.18 g, 215.82 mmol), DMF (360 ml) were added to Sub1-I-49 (23.25 g, 71.94 mmol) obtained in the above synthesis, and then21.31 g (yield: 80%) of the product was obtained by using the samemanner as described above for the synthesis of Sub 1-II-3.

(3) Synthesis of Sub 1-49

1-bromo-2-iodobenzene (17.43 g, 61.62 mmol), Pd(PPh₃)4 (1.94 g, 1.68mmol), NaOH (6.72 g, 168.05 mmol), THF (200 ml), water (100 ml) wereadded to Sub 1-II-49 (20.74 g, 56.02 mmol) obtained in the abovesynthesis, and then 15.21 g (yield: 68%) of the product was obtained byusing the same manner as described above for the synthesis of Sub 1-3.

The compound belonging to Sub 1 may be, but not limited to, thefollowing compounds, and Table 1 shows FD-MS (Field Desorption-MassSpectrometry) values of compounds belonging to Sub 1.

TABLE 1 compound FD-MS compound FD-MS Sub1-1 m/z = 245.97(C₁₂H₇BrO =247.09) Sub1-2 m/z = 398.03(C₂₄H₁₅BrO = 399.28) Sub1-3 m/z =322.00(C₁₈H₁₁BrO = 323.18) Sub1-4 m/z = 398.03(C₂₄H₁₅BrO = 399.28)Sub1-5 m/z = 403.06(C₂₄H₁₀D₅BrO = 404.31) Sub1-6 m/z =458.03(C₂₆H₁₁D₄BrOS = 459.39) Sub1-7 m/z = 505.11(C₃₂H₁₂D₇BrO = 506.44)Sub1-8 m/z = 398.03(C₂₄H₁₅BrO = 399.28) Sub1-9 m/z = 477.07(C₂₉H₁₂D₄BrNO= 478.37) Sub1-10 m/z = 438.06(C₂₇H₁₉BrO = 439.34) Sub1-11 m/z =448.05(C₂₈H₁₇BrO = 449.34) Sub1-12 m/z = 322.00(C₁₈H₁₁BrO = 323.18)Sub1-13 m/z = 398.03(C₂₄H₁₅BrO = 399.28) Sub1-14 m/z = 438.06(C₂₇H₁₉BrO= 439.34) Sub1-15 m/z = 398.03(C₂₄H₁₅BrO = 399.28) Sub1-16 m/z =245.97(C₁₂H₇BrO = 247.09) Sub1-17 m/z = 322.00(C₁₈H₁₁BrO = 323.18)Sub1-18 m/z = 323.01(C₁₈H₁₀DBrO = 324.19) Sub1-19 m/z =500.05(C₃₀H₁₇BrN₂O = 501.37) Sub1-20 m/z = 350.03(C₂₀H₁₅BrO = 351.24)Sub1-21 m/z = 406.08(C₂₄H₇D₈BrO = 407.33) Sub1-22 m/z = 322.00(C₁₈H₁₁BrO= 323.18) Sub1-23 m/z = 514.09(C₃₃H₂₃BrO = 515.44) Sub1-24 m/z =427.99(C₂₄H₁₃BrOS = 429.33) Sub1-25 m/z = 398.03(C₂₄H₁₅BrO = 399.28)Sub1-26 m/z = 245.97(C₁₂H₇BrO = 247.09) Sub1-27 m/z = 322.00(C₁₈H₁₁BrO =323.18) Sub1-28 m/z = 455.09(C₂₈H₁₀D₇BrO = 456.38) Sub1-29 m/z =326.02(C₁₈H₇D₄BrO = 327.21) Sub1-30 m/z = 372.01(C₂₂H₁₃BrO = 373.24)Sub1-31 m/z = 398.03(C₂₄H₁₅BrO = 399.28) Sub1-32 m/z = 427.99(C₂₄H₁₃BrOS= 429.33) Sub1-33 m/z = 322.00(C₁₈H₁₁BrO = 323.18) Sub1-34 m/z =372.01(C₂₂H₁₃BrO = 373.24) Sub1-35 m/z = 438.06(C₂₇H₁₉BrO = 439.34)Sub1-36 m/z = 398.03(C₂₄H₁₅BrO = 399.28) Sub1-37 m/z = 560.08(C₃₇H₂₁BrO= 561.47) Sub1-38 m/z = 379.06(C₂₁H₁₈BrNO = 380.28) Sub1-39 m/z =327.03(C₁₈H₆BrO = 328.21) Sub1-40 m/z = 322.00(C₁₈H₁₁BrO = 323.18)Sub1-41 m/z = 336.01(C₁₉H₁₃BrO = 337.21) Sub1-42 m/z =403.06(C₂₄H₁₀D₅BrO = 404.31) Sub1-43 m/z = 424.05(C₂₆H₁₇BrO = 425.32)Sub1-44 m/z = 488.04(C₃₀H₁₇BrO₂ = 489.36) Sub1-45 m/z =326.02(C₁₈H₇D₄BrO = 327.21) Sub1-46 m/z = 398.03(C₂₄H₁₅BrO = 399.28)Sub1-47 m/z = 562.09(C₃₇H₂₃BrO = 563.48) Sub1-48 m/z =479.09(C₃₀H₁₄D₅BrO = 480.41) Sub1-49 m/z = 398.03(C₂₄H₁₅BrO = 399.28)

II. Synthesis of Sub 2

Sub 2 of the Reaction Scheme 1 can be synthesized according to, but notlimited to, the reaction route of the following Reaction Scheme 12.

Synthesis Examples of compounds comprised in Sub 2 are as follows.

1. Synthesis Example of Sub 2-9

The starting materialnaphthalene-1,2,3,4,5,6,7-d7,8-(4-bromophenyl)-(13.67 g, 47.10 mmol) wasdissolved in toluene (330 ml) in a round bottom flask, and thenaniline-d5 (5.09 g, 51.81 mmol), Pd₂(dba)₃ (1.29 g, 1.41 mmol), 50%P(t-Bu)₃ (1.8 ml, 3.77 mmol), NaOt-Bu (13.58 g, 141.31 mmol) were addedand stirred at 80° C. When the reaction was completed, the reactionproduct was extracted with CH₂Cl₂ and water, and then, the organic layerwas dried with MgSO₄ and concentrated. Then, the concentrate was passedthrough silica gel column and recrystallized to obtain 10.14 g (yield:70%) of the product.

2. Synthesis Example of Sub 2-12

[1,1′-biphenyl]-4-amine (18.58 g, 109.79 mmol), Pd₂(dba)₃ (2.74 g, 2.99mmol), 50% P(t-Bu)₃ (3.9 ml, 7.98 mmol), NaOt-Bu (28.78 g, 299.43 mmol),toluene (700 ml) were added to 1-bromonaphthalene-d7 (21.37 g, 99.81mmol) obtained in the above synthesis, and then 21.43 g (yield: 71%) ofthe product was obtained by using the same manner as described above forthe synthesis of Sub 2-9.

3. Synthesis Example of Sub 2-14

1-aminonaphthalene-d7 (9.46 g, 62.99 mmol), Pd₂(dba)₃ (1.57 g, 1.72mmol), 50% P(t-Bu)₃ (2.2 ml, 4.58 mmol), NaOt-Bu (16.51 g, 171.78 mmol),toluene (400 ml) were added to 1-bromonaphthalene-d7 (12.26 g, 57.26mmol) obtained in the above synthesis, and then 10.22 g (yield: 63%) ofthe product was obtained by using the same manner as described above forthe synthesis of Sub 2-9.

4. Synthesis Example of Sub 2-15

4-(trimethylsilyl)aniline (9.38 g, 56.72 mmol), Pd₂(dba)₃ (1.42 g, 1.55mmol), 50% P(t-Bu)₃ (2.0 ml, 4.12 mmol), NaOt-Bu (14.87 g, 154.69 mmol),toluene (360 ml) were added to 2-bromonaphthalene-d7 (11.04 g, 51.56mmol) obtained in the above synthesis, and then 10.47 g (yield: 68%) ofthe product was obtained by using the same manner as described above forthe synthesis of Sub 2-9.

5. Synthesis Example of Sub 2-22

Naphthalen-2-amine (7.63 g, 53.27 mmol), Pd₂(dba)₃ (1.33 g, 1.45 mmol),50% P(t-Bu)₃ (1.9 ml, 3.87 mmol), NaOt-Bu (13.96 g, 145.28 mmol),toluene (340 ml) were added to 9-bromophenanthrene-d9 (12.89 g, 48.43mmol) obtained in the above synthesis, and then 10.34 g (yield: 65%) ofthe product was obtained by using the same manner as described above forthe synthesis of Sub 2-9.

6. Synthesis Example of Sub 2-34

[1,1′-biphenyl]-4-amine (6.93 g, 40.97 mmol), Pd2(dba)₃ (1.02 g, 1.12mmol), 50% P(t-Bu)₃ (1.5 ml, 2.98 mmol), NaOt-Bu (10.74 g, 111.75 mmol),toluene (260 ml) were added tonaphthalene-1,2,3,4,5,6,7-d7,8-(4-bromophenyl) (10.81 g, 37.25 mmol)obtained in the above synthesis, and then 10.86 g (yield: 77%) of theproduct was obtained by using the same manner as described above for thesynthesis of Sub 2-9.

7. Synthesis Example of Sub 2-43

Naphthalene-1,2,3,4,5,6,7-d7,8-(3-aminophenyl) (7.95 g, 35.14 mmol),Pd₂(dba)₃ (0.88 g, 0.96 mmol), 50% P(t-Bu)₃ (1.2 ml, 2.56 mmol), NaOt-Bu(9.21 g, 95.83 mmol), toluene (225 ml) were added tonaphthalene-1,2,3,4,5,6,7-d7,8-(3-bromophenyl) (9.27 g, 31.94 mmol)obtained in the above synthesis, and then 10.16 g (yield: 73%) of theproduct was obtained by using the same manner as described above for thesynthesis of Sub 2-9.

8. Synthesis Example of Sub 2-48

3,5-dimethoxyaniline (6.72 g, 43.89 mmol), Pd2(dba)3 (1.10 g, 1.20mmol), 50% P(t-Bu)₃ (1.6 ml, 3.19 mmol), NaOt-Bu (11.50 g, 119.71 mmol),toluene (280 ml) were added tonaphthalene-1,3,4,5,6,7,8-d7,2-(3-bromophenyl) (11.58 g, 39.90 mmol)obtained in the above synthesis, and then 9.98 g (yield: 69%) of theproduct was obtained by using the same manner as described above for thesynthesis of Sub 2-9.

The compound belonging to Sub 2 may be, but not limited to, thefollowing compounds, and Table 2 shows FD-MS values of compoundsbelonging to Sub 2.

TABLE 2 compound FD-MS compound FD-MS Sub2-1 m/z = 200.14(C₁₄H₁₂D₃N =200.29) Sub2-2 m/z = 224.14(C₁₆H₈D₅N = 224.31) Sub2-3 m/z =274.15(C₂₀H₁₀D₅N = 274.37) Sub2-4 m/z = 250.15(C₁₈H₁₀D₅N = 250.35)Sub2-5 m/z = 350.18(C₂₆H₁₄D₅N = 350.47) Sub2-6 m/z = 179.15(C₁₂H₁₀N =179.28) Sub2-7 m/z = 231.18(C₁₆HD₁₂N = 231.36) Sub2-8 m/z =255.18(C₁₈H₅D₁₀N = 255.38) Sub2-9 m/z = 307.21(C₂₂H₅D₁₂N = 307.45)Sub2-10 m/z = 305.20(C₂₂H₇D₁₀N = 305.44) Sub2-11 m/z = 252.16(C₁₈H₈D₇N =252.36) Sub2-12 m/z = 302.18(C₂₂H₁₀D₇N = 302.42) Sub2-13 m/z =356.22(C₂₆H₈D₁₁N = 356.50) Sub2-14 m/z = 283.21(C₂₀HD₁₄N = 283.43)Sub2-15 m/z = 298.19(C₁₉H₁₄D₇NSi = 298.51) Sub2-16 m/z =484.24(C₃₄H₂₀D₇NSi = 484.71) Sub2-17 m/z = 231.18(C₁₆HD₁₂N = 231.36)Sub2-18 m/z = 283.21(C₂₀HD₁₄N = 283.43) Sub2-19 m/z = 359.24(C₂₆H₅D₁₄N =359.52) Sub2-20 m/z = 304.19(C₂₂H₈D₉N = 304.43) Sub2-21 m/z =328.19(C₂₄H₈D₉N = 328.45) Sub2-22 m/z = 328.19(C₂₄H₈D₉N = 328.45)Sub2-23 m/z = 375.19(C₂₈H₁₇D₄N = 375.50) Sub2-24 m/z = 423.19(C₃₂H₁₇D₄N= 423.54) Sub2-25 m/z = 329.20(C₂₄H₁₁D₈N = 329.46) Sub2-26 m/z =330.21(C₂₄H₁₀D₉N = 330.47) Sub2-27 m/z = 339.26(C₂₄HD₁₈N = 339.53)Sub2-28 m/z = 300.17(C₂₂H₁₂D₅N = 300.41) Sub2-29 m/z = 431.25(C₃₂H₁₃D₁₀N= 431.59) Sub2-30 m/z = 300.17(C₂₂H₁₂D₅N = 300.41) Sub2-31 m/z =314.18(C₂₃H₁₄D₅N = 314.43) Sub2-32 m/z = 431.25(C₃₂H₁₃D₁₀N = 431.59)Sub2-33 m/z = 431.25(C₃₂H₁₃D₁₀N = 431.59) Sub2-34 m/z = 378.21(C₂₈H₁₄D₇N= 378.52) Sub2-35 m/z = 402.21(C₃₀H₁₄D₇N = 402.54) Sub2-36 m/z =306.21(C₂₂H₆D₁₁N = 306.44) Sub2-37 m/z = 435.27(C₃₂H₉D₁₄N = 435.62)Sub2-38 m/z = 435.27(C₃₂H₉D₁₄N = 435.62) Sub2-39 m/z = 387.27(C₂₈H₅D₁₆N= 387.57) Sub2-40 m/z = 387.27(C₂₈H₅D₁₆N = 387.57) Sub2-41 m/z =443.32(C₃₂HD₂₂N = 443.67) Sub2-42 m/z = 378.21(C₂₈H₁₄D₇N = 378.52)Sub2-43 m/z = 435.27(C₃₂H₉D₁₄N = 435.62) Sub2-44 m/z = 378.21(C₂₈H₁₄D₇N= 378.52) Sub2-45 m/z = 444.20(C₃₂H₁₃D₇FN = 444.55) Sub2-46 m/z =352.20(C₂₆H₁₂D₇N = 352.48) Sub2-47 m/z = 435.27(C₃₂H₉D₁₄N = 435.62)Sub2-48 m/z = 362.20(C₂₄H₁₄D₇NO₂ = 362.47) Sub2-49 m/z =435.27(C₃₂H₉D₁₄N = 435.62) Sub2-50 m/z = 539.33(C₄₀H₉D₁₈N = 539.76)

III. Synthesis of Final Products

Sub 1 (1 eq.) was dissolved in toluene in a round bottom flask, and Sub2 (1 eq.), Pd₂(dba)₃ (0.03 eq.), P(t-Bu)_(h) (0.08 eq.) and NaOt-Bu (3eq.) were added, then, stirring at 100□ was followed. When the reactionwas completed, the reaction product was extracted with CH₂Cl₂ and water,and then the organic layer was dried with MgSO₄ and concentrated. Then,the concentrate was passed through silica gel column and recrystallizedto obtain final product.

1. Synthesis Example of P-3

Sub 1-3 (5.42 g, 16.77 mmol) obtained in the above synthesis wasdissolved in toluene (170 ml) in a round bottom flask, and Sub 2-12(5.07 g, 16.77 mmol), Pd₂(dba)₃ (0.46 g, 0.50 mmol), 50% P(t-Bu)₃ (0.7ml, 1.34 mmol), NaOt-Bu (4.84 g, 50.31 mmol) were added, then, stirringat 100° C. was followed. When the reaction was completed, the reactionproduct was extracted with CH₂Cl₂ and water, and then the organic layerwas dried with MgSO₄ and concentrated. Then, the concentrate was passedthrough silica gel column and recrystallized to obtain 7.67 g (yield:84%) of product.

2. Synthesis Example of P-7

Sub 2-48 (5.14 g, 14.17 mmol), Pd₂(dba)₃ (0.39 g, 0.43 mmol), 50%P(t-Bu)₃ (0.6 ml, 1.13 mmol), NaOt-Bu (4.09 g, 42.51 mmol), toluene (140ml) were added to Sub 1-6 (6.51 g, 14.17 mmol) obtained in the abovesynthesis, and then 7.03 g (yield: 67%) of the product was obtained byusing the same manner as described above for the synthesis of thecompound P-3.

3. Synthesis Example of P-11

Sub 2-9 (4.60 g, 14.98 mmol), Pd₂(dba)₃ (0.41 g, 0.45 mmol), 50%P(t-Bu)₃ (0.6 ml, 1.20 mmol), NaOt-Bu (4.32 g, 44.93 mmol), toluene (150ml) were added to Sub 1-10 (6.58 g, 14.98 mmol) obtained in the abovesynthesis, and then 7.48 g (yield: 75%) of the product was obtained byusing the same manner as described above for the synthesis of thecompound P-3.

4. Synthesis Example of P-25

Sub 2-34 (5.69 g, 15.04 mmol), Pd₂(dba)₃ (0.41 g, 0.45 mmol), 50%P(t-Bu)₃ (0.6 ml, 1.20 mmol), NaOt-Bu (4.34 g, 45.11 mmol), toluene (150ml) were added to Sub 1-22 (4.86 g, 15.04 mmol) obtained in the abovesynthesis, and then 7.66 g (yield: 82%) of the product was obtained byusing the same manner as described above for the synthesis of thecompound P-3.

5. Synthesis Example of P-27

Sub 2-14 (4.57 g, 16.14 mmol), Pd₂(dba)₃ (0.44 g, 0.48 mmol), 50%P(t-Bu)₃ (0.6 ml, 1.29 mmol), NaOt-Bu (4.65 g, 48.42 mmol), toluene (160ml) were added to Sub 1-24 (6.93 g, 16.14 mmol) obtained in the abovesynthesis, and then 7.24 g (yield: 71%) of the product was obtained byusing the same manner as described above for the synthesis of thecompound P-3.

6. Synthesis Example of P-30

Sub 2-43 (7.40 g, 17.00 mmol), Pd₂(dba)₃ (0.47 g, 0.51 mmol), 50%P(t-Bu)₃ (0.7 ml, 1.36 mmol), NaOt-Bu (4.90 g, 50.99 mmol), toluene (170ml) were added to Sub 1-26 (4.20 g, 17.00 mmol) obtained in the abovesynthesis, and then 7.67 g (yield: 75%) of the product was obtained byusing the same manner as described above for the synthesis of thecompound P-3.

7. Synthesis Example of P-34

Sub 2-22 (5.78 g, 17.61 mmol), Pd₂(dba)₃ (0.48 g, 0.53 mmol), 50%P(t-Bu)₃ (0.7 ml, 1.41 mmol), NaOt-Bu (5.08 g, 52.82 mmol), toluene (175ml) were added to Sub 1-27 (5.69 g, 17.61 mmol) obtained in the abovesynthesis, and then 7.74 g (yield: 77%) of the product was obtained byusing the same manner as described above for the synthesis of thecompound P-3.

8. Synthesis Example of P-41

Sub 2-12 (4.79 g, 15.85 mmol), Pd2(dba)₃ (0.44 g, 0.48 mmol), 50%P(t-Bu)₃ (0.6 ml, 1.27 mmol), NaOt-Bu (4.57 g, 47.56 mmol), toluene (160ml) were added to Sub 1-31 (6.33 g, 15.85 mmol) obtained in the abovesynthesis, and then 7.87 g (yield: 80%) of the product was obtained byusing the same manner as described above for the synthesis of thecompound P-3.

9. Synthesis Example of P-58

Sub 2-15 (5.66 g, 18.96 mmol), Pd₂(dba)₃ (0.52 g, 0.57 mmol), 50%P(t-Bu)₃ (0.7 ml, 1.52 mmol), NaOt-Bu (5.47 g, 56.88 mmol), toluene (190ml) were added to Sub 1-49 (7.57 g, 18.96 mmol) obtained in the abovesynthesis, and then 7.60 g (yield: 65%) of the product was obtained byusing the same manner as described above for the synthesis of thecompound P-3.

The FD-MS values of compounds P-1 to P-60 of the present inventionprepared according to the above synthesis examples are shown in Table 3below.

TABLE 3 compound FD-MS compound FD-MS P-1 m/z = 568.26(C₄₂H₂₄D₅NO =568.72) P-2 m/z = 597.29(C₄₄H₁₉D₁₀NO = 597.77) P-3 m/z =544.25(C₄₀H₂₀D₇NO = 544.69) P-4 m/z = 620.28(C₄₆H₂₄D₇NO = 620.79) P-5m/z = 657.37(C₄₈H₁₅D₁₈NO = 657.89) P-6 m/z = 630.35(C₄₆H₁₄D₁₇NO =630.85) P-7 m/z = 740.30(C₅₀H₂₄D₁₁NO₃S = 740.95) P-8 m/z =708.39(C₅₂H₁₂D₂₁NO = 708.95) P-9 m/z = 647.31(C₄₈H₂₅D₈NO = 647.83) P-10m/z = 697.31(C₅₁H₂₃D₉N₂O = 697.87) P-11 m/z = 665.35(C₄₉H₂₃D₁₂NO =665.88) P-12 m/z = 620.28(C₄₆H₂₄D₇NO = 620.79) P-13 m/z =601.31(C₄₄H₁₅D₁₄NO = 601.79) P-14 m/z = 693.30(C₅₂H₃₁D₄NO = 693.87) P-15m/z = 793.41(C₅₉H₂₇D₁₄NO = 794.05) P-16 m/z = 646.30(C₄₈H₂₂D₉NO =646.82) P-17 m/z = 541.23(C₄₀H₂₃D₄NO = 541.67) P-18 m/z =610.24(C₄₄H₁₉D₇FNO = 610.72) P-19 m/z = 644.28(C₄₈H₂₄D₇NO = 644.81) P-20m/z = 629.34(C₄₆H₁₅D₁₆NO = 629.84) P-21 m/z = 666.27(C₅₀H₂₆D₅NO =666.82) P-22 m/z = 754.34(C₅₄H₃₄D₇NOSi = 755.04) P-23 m/z =620.27(C₄₄H₂₈D₃N₃O = 620.75) P-24 m/z = 505.31(C₃₆H₇D₁₈NO = 505.70) P-25m/z = 620.28(C₄₆H₂₄D₇NO = 620.79) P-26 m/z = 734.33(C₅₅H₃₄D₅NO = 734.94)P-27 m/z = 631.27(C₄₄H₁₃D₁₄NOS = 631.84) P-28 m/z = 753.38(C₅₆H₂₃D₁₄NO =753.99) P-29 m/z = 472.25(C₃₄H₁₂D₁₁NO = 472.62) P-30 m/z =601.31(C₄₄H₁₅D₁₄NO = 601.79) P-31 m/z = 705.37C₅₂H₁₅D₁₈NO = 705.94) P-32m/z = 624.31(C₄₆H₂₀D₁₁NO = 624.81) P-33 m/z = 473.25(C₃₄H₁₁D₁₂NO =473.63) P-34 m/z = 570.27(C₄₂H₁₈D₉NO = 570.73) P-35 m/z =620.28(C₄₆H₂₄D₇NO = 620.79) P-36 m/z = 677.34(C₅₀H₁₉D₁₄NO = 677.89) P-37m/z = 753.38(C₅₆H₂₃D₁₄NO = 753.99) P-38 m/z = 685.39(C₅₀H₁₁D₂₂NO =685.94) P-39 m/z = 673.32(C₅₀H₂₃D₁₀NO = 673.86) P-40 m/z =644.28(C₄₈H₂₄D₇NO = 644.81) P-41 m/z = 620.28(C₄₆H₂₄D₇NO = 620.79) P-42m/z = 572.20(C₄₀H₂₀D₅NOS = 572.73) P-43 m/z = 677.34(C₅₀H₁₉D₁₄NO =677.89) P-44 m/z = 723.33(C₅₄H₂₅D₁₀NO = 723.92) P-45 m/z =696.32(C₅₂H₂₈D₇NO = 696.88) P-46 m/z = 793.41(C₅₉H₂₇D₁₄NO = 794.05) P-47m/z = 785.35(C₅₉H₂₇D₁₀NO = 785.99) P-48 m/z = 573.28(C₄₁H₂₇D₅N₂O =573.74) P-49 m/z = 577.31(C₄₂H₁₅D₁₄NO = 577.77) P-50 m/z =677.34(C₅₀H₁₉D₁₄NO = 677.89) P-51 m/z = 629.34(C₄₆H₁₅D₁₆NO = 629.84)P-52 m/z = 596.28(C₄₄H₂₀D₉NO = 596.76) P-53 m/z = 578.32(C₄₂H₁₄D₁₅NO =578.78) P-54 m/z = 632.25(C₄₆H₂₄D₅NO₂ = 632.76) P-55 m/z =570.27(C₄₂H₂₆D₅NO = 570.73) P-56 m/z = 648.31(C₄₈H₂₄D₉NO = 648.84) P-57m/z = 755.39(C₅₆H₂₁D₁₆NO = 756.00) P-58 m/z = 616.29(C₄₃H₂₈D₇NOSi =616.87) P-59 m/z = 713.35(C₅₃H₂₃D₁₂NO = 713.93) P-60 m/z =705.37(C₅₂H₁₉D₁₆NO = 705.94)

In the above, even though an exemplary synthesis example of the presentinvention represented by the Formula 1 are described, all of them arebased on Buchwald-Hartwig cross coupling reaction, Pd(II)-catalyzedoxidative cyclization reaction (Org. Lett. 2011, 13, 5504), Miyauraboration reaction and Suzuki cross-coupling reaction. It will beunderstood by those skilled in the art that the above reaction proceedseven when other substituents (substituents of R¹, R², L¹ to L³, Ar¹,Ar², m and n and the like) defined in Formula 1 are bonded, in additionto the substituents described in the specific synthesis example.

For example, the reaction of Sub 1 and Sub 2→Final Product in ReactionScheme 1, and the reaction of the starting material→Sub 2 in ReactionScheme 12 are based on Buchwald-Hartwig cross coupling reaction, thereaction of the starting material→Sub 1-I/Sub1 (L¹=single bond) inReaction Scheme 2 is based on Pd(II)-catalyzed oxidative cyclizationreaction, and the reaction of Sub 1-I→Sub 1-II in Reaction Scheme 2 isbased on Miyaura boration reaction. Further, the reaction of Sub1-II→Sub 1 in Reaction Scheme 2 is based on Suzuki cross-couplingreaction. The above reactions will proceed even if a substituent notspecifically mentioned is attached.

Fabrication and Evaluation of Organic Electronic Element

Example I-1 Green OLED (A Hole Transport Layer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as ahole transport layer material.

First, an ITO layer (anode) was formed on a glass substrate, and then4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter,“2-TNATA”) was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm. Subsequently, compound P-1 ofthe present invention was vacuum-deposited with a thickness of 60 nm onthe hole injection layer to form a hole transport layer. Subsequently, alight emitting layer with a thickness of 30 nm was formed on the holetransport layer by using 4,4′-N,N′-dicarbazole-biphenyl (hereinafter,“CBP”) as a host material and tris(2-phenylpyridine)-iridium(hereinafter, “Ir(ppy)₃)”) as a dopant material in a weight ratio of90:10.

Next, ((1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAlq”) was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, andtris(8-quinolinolato)aluminum (hereinafter, “Alq₃”) was formed with athickness of 40 nm to form an electron transport layer. Next,halogenated alkali metal LiF was deposited with a thickness of 0.2 nm onthe electron transport layer to form an electron injection layer, andthen Al was deposited with a thickness of 150 nm on the electroninjection layer to form a cathode. In this way, the OLED was completed.

Example I-2 to Example I-43 Green OLED (A Hole Transport Layer)

The OLEDs were fabricated in the same manner as described in Example I-1except that the compounds P-2 to P-60 of the present invention describedin Table 4 instead of the compound P-1 of the present invention wereused as the hole transport layer material.

Comparative Example I-1 to Comparative Example 1-5

The OLEDs were fabricated in the same manner as described in Example I-1except that the following Comparative Compounds 1 to 5 instead of thecompound P-1 of the present invention were each used as the holetransport layer material.

Electroluminescence (EL) characteristics were measured with a PR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples I-1 to I-43 of the present invention andComparative Examples I-1 to I-5. And, the T95 life time was measuredusing a life time measuring apparatus manufactured by Macscience Inc. atreference brightness of 5000 cd/m². The measurement results are shown inTable 4 below.

TABLE 4 Current Voltage Density Brightness Efficiency Lifetime CIEcompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y comp. Ex(I-1) comp. Com16.0 21.5 5000 23.3 57.2 0.32 0.61 comp. Ex(I-2) comp. Com2 5.9 18.4 500027.2 73.2 0.32 0.62 comp. Ex(I-3) comp. Com3 5.8 17.8 5000 28.1 76.80.33 0.62 comp. Ex(I-4) comp. Com4 5.8 17.5 5000 28.5 80.7 0.33 0.61comp. Ex(I-5) comp. Com5 5.8 15.7 5000 31.9 82.3 0.33 0.62 Ex.(I-1)Com.(P-1) 5.5 13.6 5000 36.7 129.3 0.33 0.62 Ex.(I-2) Com.(P-2) 5.5 13.95000 36.1 134.1 0.33 0.62 Ex.(I-3) Com.(P-3) 5.4 13.3 5000 37.7 140.30.33 0.61 Ex.(I-4) Com.(P-4) 5.5 13.0 5000 38.5 140.7 0.33 0.62 Ex.(I-5)Com.(P-5) 5.4 13.6 5000 36.9 128.0 0.33 0.61 Ex.(I-6) Com.(P-6) 5.5 13.35000 37.7 136.4 0.33 0.61 Ex.(I-7) Com.(P-9) 5.5 13.6 5000 36.8 130.00.33 0.61 Ex.(I-8) Com.(P-11) 5.4 13.2 5000 37.9 139.4 0.33 0.61Ex.(I-9) Com.(P-13) 5.5 13.2 5000 37.8 136.3 0.33 0.61 Ex.(I-10)Com.(P-14) 5.5 13.4 5000 37.2 133.4 0.33 0.62 Ex.(I-11) Com.(P-15) 5.513.1 5000 38.1 137.5 0.33 0.61 Ex.(I-12) Com.(P-16) 5.5 13.6 5000 36.8135.4 0.33 0.61 Ex.(I-13) Com.(P-17) 5.5 14.5 5000 34.5 128.5 0.33 0.61Ex.(I-14) Com.(P-19) 5.6 14.1 5000 35.4 132.7 0.33 0.61 Ex.(I-15)Com.(P-20) 5.5 13.4 5000 37.2 136.0 0.33 0.61 Ex.(I-16) Com.(P-21) 5.514.5 5000 34.5 132.3 0.33 0.61 Ex.(I-17) Com.(P-24) 5.6 14.0 5000 35.8125.7 0.33 0.62 Ex.(I-18) Com.(P-25) 5.5 13.8 5000 36.1 132.6 0.33 0.62Ex.(I-19) Com.(P-27) 5.5 14.1 5000 35.3 130.5 0.33 0.62 Ex.(I-20)Com.(P-28) 5.5 14.0 5000 35.8 130.7 0.33 0.62 Ex.(I-21) Com.(P-29) 5.413.2 5000 37.8 137.9 0.33 0.62 Ex.(I-22) Com.(P-30) 5.4 13.2 5000 37.9140.5 0.33 0.61 Ex.(I-23) Com.(P-31) 5.4 13.0 5000 38.5 142.5 0.33 0.62Ex.(I-24) Com.(P-32) 5.4 12.6 5000 39.7 147.2 0.33 0.62 Ex.(I-25)Com.(P-33) 5.5 13.0 5000 38.5 142.3 0.33 0.61 Ex.(I-26) Com.(P-34) 5.413.0 5000 38.6 141.0 0.33 0.61 Ex.(I-27) Com.(P-35) 5.4 12.5 5000 39.9148.9 0.33 0.62 Ex.(I-28) Com.(P-36) 5.5 12.8 5000 39.1 144.0 0.33 0.62Ex.(I-29) Com.(P-37) 5.5 13.0 5000 38.4 140.5 0.33 0.61 Ex.(I-30)Com.(P-38) 5.4 12.7 5000 39.3 144.2 0.33 0.62 Ex.(I-31) Com.(P-39) 5.413.1 5000 38.2 142.2 0.33 0.62 Ex.(I-32) Com.(P-41) 5.5 13.0 5000 38.4141.4 0.33 0.62 Ex.(I-33) Com.(P-42) 5.4 12.9 5000 38.6 140.3 0.33 0.62Ex.(I-34) Com.(P-43) 5.4 13.0 5000 38.5 141.1 0.33 0.61 Ex.(I-35)Com.(P-45) 5.4 13.0 5000 38.4 140.5 0.33 0.62 Ex.(I-36) Com.(P-46) 5.513.0 5000 38.4 142.3 0.33 0.62 Ex.(I-37) Com.(P-49) 5.6 14.8 5000 33.7124.9 0.33 0.61 Ex.(I-38) Com.(P-50) 5.6 14.3 5000 34.9 129.7 0.33 0.62Ex.(I-39) Com.(P-51) 5.6 14.0 5000 35.7 136.6 0.33 0.62 Ex.(I-40)Com.(P-52) 5.6 14.6 5000 34.2 126.4 0.33 0.62 Ex.(I-41) Com.(P-53) 5.514.7 5000 33.9 124.6 0.33 0.62 Ex.(I-42) Com.(P-59) 5.5 14.6 5000 34.2127.0 0.33 0.61 Ex.(I-43) Com.(P-60) 5.6 14.5 5000 34.4 126.9 0.33 0.62

From the results of the above table 4, it can be confirmed that luminousefficiency and lifetime of OLED are improved when the compound of thepresent invention is used as material of a hole transport layer.Particularly, Comparative Example I-2 to Comparative Example I-5 usingComparative compounds 2 to 5 in which an arylamine group is bonded todibenzofuran core via a linkage (comprising a single bond) exhibitedhigher luminous efficiency than Comparative Example I-1 usingComparative compound 1 that is NPB widely used. Further, Example I-1 toExample 1-43 using the compound of the present invention in which anarylamine group substituted with deuterium is bonded to dibenzofurancore via a linkage (comprising a single bond) exhibited lower drivingvoltage, higher luminous efficiency and improved lifetime, comparing toComparative Example I-2 to Comparative Example I-5.

These results show that the results are different depending on whetheror not an arylamine group is substituted with deuterium. When anarylamine group is substituted with deuterium, the molecular hardcorevolume is reduced as the zero point energy, that is, the energy of thebottom state, is lowered and the bond length of carbon and deuteriumbecomes shorter than the bond length of carbon and hydrogen. As aresult, the electrical polarizability can be reduced and intermolecularinteraction can be weakened, thereby increasing the film volume.

This property can produce an effect of lowering the crystallinity of thethin film, that is, an amorphous state, and this amorphous state canreduce the grain boundary through isotropic and homogeneouscharacteristics. As a result, it is considered that the charge flow,that is, the hole mobility is increased, thereby making a very effectivestate in which the driving voltage of the organic electroluminescentdevice can be lowered and the lifetime can be improved.

Example II-1 Green OLED (An Emission-Auxiliary Layer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as anemission-auxiliary layer material.

First, an ITO layer (anode) was formed on a glass substrate, and a filmof 2-TNATA was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm. Subsequently, Comparativecompound 1 was vacuum-deposited with a thickness of 60 nm on the holeinjection layer to form a hole transport layer. Subsequently, a film ofthe compound P-1 of the present invention was vacuum-deposited on thehole transport layer to form a emission-auxiliary layer with a thicknessof 20 nm. A light emitting layer with a thickness of 30 nm was depositedon the emission-auxiliary layer by using the CBP as a host material andIr(ppy)₃ as a dopant material in a weight ratio of 90:10.

Next, a film of BAlq was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film ofAlq₃ was formed with a thickness of 40 nm to form an electron transportlayer. Next, LiF as halogenated alkali metal was deposited with athickness of 0.2 nm on the electron transport layer to form an electroninjection layer, and then Al was deposited with a thickness of 150 nm onthe electron injection layer to form a cathode. In this way, the OLEDwas completed.

Example II-2 to Example II-45 Green OLED (An Emission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in ExampleII-1 except that the compounds P-3 to P-60 of the present inventiondescribed in Table 5, instead of the compound P-1 of the presentinvention, were used as an emission-auxiliary layer material.

Comparative Example II-1

The OLED was fabricated in the same manner as described in Example II-1except that an emission-auxiliary layer was not formed.

Comparative Example II-2 to Comparative Example II-5 Green OLED (AnEmission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in ExampleII-1 except that the Comparative compounds 2 to 5, instead of thecompound P-1 of the present invention, were used as anemission-auxiliary layer material.

Example II-46 Green OLED (An Emission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in ExampleII-1 except that Comparative compound 6 described in Table 6, instead ofComparative compound 1, was used as a hole transport layer material.

Example II-47 to Example II-75 Green OLED (An Emission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in ExampleII-46 except that the compounds P-3 to P-60 of the present inventiondescribed in Table 6, instead of the compound P-1 of the presentinvention, were used as an emission-auxiliary layer material.

Comparative Example II-6

The OLED was fabricated in the same manner as described in Example II-46except that an emission-auxiliary layer was not formed.

Comparative Example II-7 to Comparative Example II-10 Green OLED (AnEmission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in ExampleII-46 except that the Comparative compounds 2 to 5 described in Table 6,instead of the compound P-1 of the present invention, were used as anemission-auxiliary layer material.

Electroluminescence (EL) characteristics were measured with a PR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples II-1 to II-75 of the present invention andComparative Examples II-1 to II-10. And, the T95 life time was measuredusing a life time measuring apparatus manufactured by Macscience Inc. atreference brightness of 5000 cd/m². The measurement results are shown inTables 5 and 6 below.

TABLE 5 Current Voltage Density Brightness Efficiency Lifetime HTL com.EAL com. (V) (mA/cm²) (cd/m²) (cd/A) T(95) comp. Ex(II-1) comp. Com1 —6.0 21.5 5000 23.3 57.2 comp. Ex(II-2) comp. Com1 comp. Com2 6.4 14.35000 35.1 98.1 comp. Ex(II-3) comp. Com1 comp. Com3 6.4 13.7 5000 36.6101.4 comp. Ex(II-4) comp. Com1 comp. Com4 6.4 13.6 5000 36.7 105.5comp. Ex(II-5) comp. Com1 comp. Com5 6.3 12.6 5000 39.8 116.5 Ex.(II-l)comp. Com1 Com.(P-1) 6.2 11.6 5000 43.2 147.0 Ex.(II-2) comp. Com1Com.(P-3) 6.1 11.3 5000 44.3 150.2 Ex.(II-3) comp. Com1 Com.(P-4) 6.211.0 5000 45.3 156.6 Ex.(II-4) comp. Com1 Com.(P-5) 6.3 11.4 5000 43.8142.1 Ex.(II-5) comp. Com1 Com.(P-6) 6.2 11.3 5000 44.4 151.6 Ex.(II-6)comp. Com1 Com.(P-9) 6.2 11.3 5000 44.2 146.5 Ex.(II-7) comp. Com1Com.(P-11) 6.1 11.2 5000 44.8 154.8 Ex.(II-8) comp. Com1 Com.(P-13) 6.211.3 5000 44.4 153.4 Ex.(II-9) comp. Com1 Com.(P-14) 6.3 11.4 5000 44.0148.4 Ex.(II-10) comp. Com1 Com.(P-15) 6.2 11.2 5000 44.7 152.2Ex.(II-11) comp. Com1 Com.(P-16) 6.3 11.3 5000 44.1 147.7 Ex.(II-12)comp. Com1 Com.(P-17) 6.3 11.7 5000 42.8 146.3 Ex.(II-13) comp. Com1Com.(P-18) 6.3 11.6 5000 43.1 150.2 Ex.(II-14) comp. Com1 Com.(P-19) 6.311.3 5000 44.2 150.8 Ex.(II-15) comp. Com1 Com.(P-20) 6.2 11.0 5000 45.5157.8 Ex.(II-16) comp. Com1 Com.(P-25) 6.1 11.3 5000 44.3 153.6Ex.(II-17) comp. Com1 Com.(P-27) 6.3 11.4 5000 43.8 148.4 Ex.(II-18)comp. Com1 Com.(P-28) 6.2 11.4 5000 43.8 148.9 Ex.(II-19) comp. Com1Com.(P-29) 6.2 11.3 5000 44.4 153.9 Ex.(II-20) comp. Com1 Com.(P-30) 6.211.2 5000 44.8 154.9 Ex.(II-21) comp. Com1 Com.(P-31) 6.1 11.1 5000 45.2151.9 Ex.(II-22) comp. Com1 Com.(P-32) 6.1 10.7 5000 46.8 160.2Ex.(II-23) comp. Com1 Com.(P-33) 6.2 11.1 5000 45.2 150.1 Ex.(II-24)comp. Com1 Com.(P-34) 6.2 10.9 5000 45.9 150.1 Ex.(II-25) comp. Com1Com.(P-35) 6.1 10.6 5000 47.2 162.9 Ex.(II-26) comp. Com1 Com.(P-36) 6.110.9 5000 45.9 158.3 Ex.(II-27) comp. Com1 Com.(P-37) 6.1 11.0 5000 45.6153.6 Ex.(II-28) comp. Com1 Com.(P-38) 6.1 10.8 5000 46.2 156.0Ex.(II-29) comp. Com1 Com.(P-39) 6.1 11.0 5000 45.6 151.2 Ex.(II 30)comp. Com1 Com.(P-40) 6.2 11.2 5000 44.5 152.9 Ex.(II-31) comp. Com1Com.(P-41) 6.2 11.1 5000 45.2 150.9 Ex.(II-32) comp. Com1 Com.(P-42) 6.111.0 5000 45.6 152.3 Ex.(II-33) comp. Com1 Com.(P-43) 6.2 10.9 5000 45.9152.9 Ex.(II-34) comp. Com1 Com.(P-44) 6.1 11.1 5000 44.9 152.2Ex.(II-35) comp. Com1 Com.(P-45) 6.2 10.9 5000 45.8 155.0 Ex.(II-36)comp. Com1 Com.(P-46) 6.1 11.0 5000 45.5 154.6 Ex.(II-37) comp. Com1Com.(P-47) 6.2 11.2 5000 44.7 155.0 Ex.(II-38) comp. Com1 Com.(P-50) 6.311.6 5000 43.3 147.3 Ex.(II-39) comp. Com1 Com.(P-51) 6.3 11.4 5000 43.9151.4 Ex.(II-40) comp. Com1 Com.(P-52) 6.3 11.8 5000 42.3 146.6Ex.(II-41) comp. Com1 Com.(P-54) 6.3 11.8 5000 42.3 142.6 Ex.(II-42)comp. Com1 Com.(P-57) 6.3 11.9 5000 42.1 143.2 Ex.(II-43) comp. Com1Com.(P-58) 6.3 11.9 5000 42.0 146.8 Ex.(II-44) comp. Com1 Com.(P-59) 6.311.8 5000 42.6 146.6 Ex.(II-45) comp. Com1 Com.(P-60) 6.3 11.7 5000 42.6146.0

TABLE 6 Current Voltage Density Brightness Efficiency Lifetime HTL com.EAL com. (V) (mA/cm²) (cd/m²) (cd/A) T(95) comp. Ex(II-6) comp. Com6 —5.0 14.3 5000 35.0 97.3 comp. Ex(II-7) comp. Com6 comp. Com2 5.4 13.45000 37.2 115.7 comp. Ex(II-8) comp. Com6 comp. Com3 5.3 13.0 5000 38.4120.1 comp. Ex(II-9) comp. Com6 comp. Com4 5.3 12.9 5000 38.9 124.6comp. Ex(II-10) comp. Com6 comp. Com5 5.3 12.0 5000 41.7 131.4Ex.(II-46) comp. Com6 Com.(P-1) 5.3 10.8 5000 46.1 158.0 Ex.(II-47)comp. Com6 Com.(P-3) 5.1 10.4 5000 48.0 167.9 Ex.(II-48) comp. Com6Com.(P-4) 5.1 10.4 5000 48.0 171.0 Ex.(II-49) comp. Com6 Com.(P-6) 5.110.5 5000 47.5 167.3 Ex.(II-50) comp. Com6 Com.(P-11) 5.2 10.4 5000 48.0167.0 Ex.(II-51) comp. Com6 Com.(P-13) 5.2 10.5 5000 47.5 165.9Ex.(II-52) comp. Com6 Com.(P-15) 5.2 10.5 5000 47.6 166.2 Ex.(II-53)comp. Com6 Com.(P-19) 5.2 10.7 5000 46.9 160.9 Ex.(II-54) comp. Com6Com.(P-20) 5.2 10.4 5000 48.1 169.2 Ex.(II-55) comp. Com6 Com.(P-25) 5.210.4 5000 48.0 167.6 Ex.(II-56) comp. Com6 Com.(P-27) 5.2 10.6 5000 47.4161.0 Ex.(II-57) comp. Com6 Com.(P-28) 5.3 10.6 5000 47.2 164.3Ex.(II-58) comp. Com6 Com.(P-30) 5.2 10.5 5000 47.5 166.4 Ex.(II-59)comp. Com6 Com.(P-31) 5.2 10.3 5000 48.7 164.8 Ex.(II-60) comp. Com6Com.(P-32) 5.1 10.0 5000 50.2 175.4 Ex.(II-61) comp. Com6 Com.(P-33) 5.110.3 5000 48.4 164.8 Ex.(II-62) comp. Com6 Com.(P-34) 5.1 10.3 5000 48.4168.2 Ex.(II-63) comp. Com6 Com.(P-35) 5.1 9.9 5000 50.5 176.5Ex.(II-64) comp. Com6 Com.(P-36) 5.1 10.2 5000 49.0 170.5 Ex.(II-65)comp. Com6 Com.(P-37) 5.2 10.4 5000 48.3 167.2 Ex.(II-66) comp. Com6Com.(P-38) 5.1 10.2 5000 48.8 170.1 Ex.(II-67) comp. Com6 Com.(P-39) 5.110.3 5000 48.7 168.2 Ex.(II-68) comp. Com6 Com.(P-41) 5.2 10.3 5000 48.4168.2 Ex.(II-69) comp. Com6 Com.(P-42) 5.2 10.3 5000 48.7 168.1Ex.(II-70) comp. Com6 Com.(P-43) 5.2 10.3 5000 48.8 167.6 Ex.(II-71)comp. Com6 Com.(P-45) 5.1 10.3 5000 48.4 164.3 Ex.(II-72) comp. Com6Com.(P-46) 5.2 10.3 5000 48.5 167.6 Ex.(II-73) comp. Com6 Com.(P-50) 5.310.8 5000 46.4 164.6 Ex.(II-74) comp. Com6 Com.(P-51) 5.3 10.7 5000 46.6166.5 Ex.(II-75) comp. Com6 Com.(P-60) 5.3 10.9 5000 45.7 156.5

Example III-1 Blue Organic Light Emitting Diode (Emission-AuxiliaryLayer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as anemission-auxiliary layer material. First, an ITO layer (anode) wasformed on a glass substrate, and 2-TNATA was vacuum-deposited on the ITOlayer to form a hole injection layer with a thickness of 60 nm.Subsequently, the Comparative compound 6 was vacuum-deposited with athickness of 60 nm on the hole injection layer to form a hole transportlayer. Next, the inventive compound P-4 was vacuum-deposited with athickness of 20 nm on the hole transport layer to form anemission-auxiliary layer. Thereafter, a light emitting layer with athickness of 30 nm was deposited on the emission-auxiliary layer bydoping the emission-auxiliary layer with9,10-di(naphthalen-2-yl)anthracene (hereinafter abbreviated as “ADN”) asa host material and BD-052X (made by Idemitsu kosan) as a dopantmaterial in a weight ratio of 96:4. Subsequently, BAlq wasvacuum-deposited with a thickness of 10 nm on the light emitting layerto form a hole blocking layer, and then a film of Alq₃ was formed with athickness of 40 nm to form an electron injection layer. Subsequently,LiF as halogenated alkali metal was deposited with a thickness of 0.2 nmon the electron injection layer, and then Al was deposited with athickness of 150 nm thereon to form a cathode. In this way, an OLED wascompleted.

Example III-2 to Example III-12 Blue OLED (An Emission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in ExampleIII-1 except that the compounds P-6 to P-51 of the present inventiondescribed in Table 7, instead of the compound P-4 of the presentinvention, were used as an emission-auxiliary layer material.

Comparative Example III-1

The OLED was fabricated in the same manner as described in Example III-1except that an emission-auxiliary layer was not formed.

Comparative Example IIII-2 to Comparative Example III-4 Blue OLED (AnEmission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in ExampleIII-1 except that the Comparative compounds 3 to 5 described in Table 7,instead of the compound P-4 of the present invention, were used as anemission-auxiliary layer material.

Electroluminescence (EL) characteristics were measured with a PR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples III-1 to III-12 of the present invention andComparative Examples III-1 to III-4. And, the T95 life time was measuredusing a life time measuring apparatus manufactured by Macscience Inc. atreference brightness of 500 cd/m². The measurement results are shown inTable 7 below.

TABLE 7 Current Voltage Density Brightness Efficiency Lifetime HTL com.EAL com. (V) (mA/cm2) (cd/m2) (cd/A) T(95) comp. Ex(III-1) comp. Com6 —4.2 12.2 500 4.1 95.8 comp. Ex(III-2) comp. Com6 comp. Com3 4.4 7.6 5006.6 109.1 comp. Ex(III-3) comp. Com6 comp. Com4 4.4 7.5 500 6.6 116.0comp. Ex(III-4) comp. Com6 comp. Com5 4.3 7.2 500 6.9 120.7 Ex.(III-1)comp. Com6 Com.(P-4) 4.4 6.8 500 7.4 164.2 Ex.(III-2) comp. Com6Com.(P-6) 4.4 6.7 500 7.5 161.9 Ex.(III-3) comp. Com6 Com.(P-11) 4.4 6.7500 7.4 162.1 Ex.(III-4) comp. Com6 Com.(P-20) 4.4 6.7 500 7.4 164.3Ex.(III-5) comp. Com6 Com.(P-25) 4.3 6.7 500 7.4 159.6 Ex.(III-6) comp.Com6 Com.(P-32) 4.3 6.6 500 7.6 170.2 Ex.(III-7) comp. Com6 Com.(P-33)4.4 6.7 500 7.5 164.7 Ex.(III-8) comp. Com6 Com.(P-35) 4.3 6.6 500 7.6172.9 Ex.(III-9) comp. Com6 Com.(P-36) 4.3 6.7 500 7.5 168.6 Ex.(III-10)comp. Com6 Com.(P-38) 4.3 6.6 500 7.5 167.7 Ex.(III-11) comp. Com6Com.(P-41) 4.3 6.7 500 7.4 164.8 Ex.(III-12) comp. Com6 Com.(P-51) 4.46.8 500 7.3 156.6

From the results shown in Tables 5 to 7, it can be seen that theluminous efficiency and lifetime of the organic electroluminescentdevice are remarkably improved when compounds of the present inventionwere used as an emission-auxiliary layer material, compared with theorganic electroluminescent device of Comparative Example II-1 toComparative Example III-4.

From these results, it is confirmed that luminescent efficiency andlifetime of device are improved when Comparative Compounds 2 to 5 andthe compound of the present invention are used as an emission-auxiliarylayer material, among them, particularly the compound of the presentinvention, compared with device not having an emission-auxiliary layer.

It can be confirmed that the structure in which an arylamine groupsubstituted with deuterium is bonded to dibenzofuran core via a linkage(comprising a single bond) acts as a major factor in improving theperformance of the device in the light-emitting auxiliary layer (greenphosphorescence, blue fluorescence) as well as in the hole transportlayer. Also, it is confirmed that the compound of the present inventionused as the light emitting auxiliary layer material has a deep HOMOenergy level and a high T1 value, thereby maintaining the charge balancein the light emitting layer and performing an effective electronicblocking function, as a result, the light emitting efficiency andlifetime are improved.

Further, it can be confirmed that the planarity of the molecules isfurther increased when 1 to 2 substituents having planarity areintroduced into the amine group of the compound of the presentinvention, and the packing density is increased, thereby reducing theJoule heat generated when the device is driven, as a result, thelifetime is remarkably increased due to the high thermal stability. Itis considered that this is because the substituent having planarity isnot introduced excessively and within an appropriate range, so that therise of the driving voltage due to the trap phenomenon hardly occurs andthe improvement of the heat resistance is more effective.

Accordingly, the compound of the present invention can provide aneffective electron blocking ability and a hole transporting ability, andthe compound of the present invention can lower the driving voltage ofthe device, increase the luminous efficiency, have high heat resistance,and improve the color purity and lifetime.

In addition, in the evaluation results of the device fabricationdescribed above, even though the characteristics of devise have beendescribed when the compound of the present invention is used as materialof only one layer of the hole transport layer and an emission-auxiliarylayer, the compound of the present invention can be used as material ofboth the hole transport layer and an emission-auxiliary layer.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

The invention claimed is:
 1. A compound of Formula 2 or 3:

wherein: R¹ and R² are each independently selected from the groupconsisting of deuterium, halogen, a cyano group, a nitro group, a C₆-C₆₀aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxyl group, and a C₆-C₃₀ aryloxyl group,wherein the aryl, fluorenyl, heterocyclic, fused ring, alkyl, alkenyl,alkynyl, alkoxy or aryloxy group may be each optionally substituted withone or more substituents selected from the group consisting ofdeuterium, halogen, a silane group substituted or unsubstituted with aC₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a cyanogroup, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group,a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, afluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, aC₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀arylalkenyl group, m is an integer of 0 to 4, and when m is an integerof 2 or more, R¹s may be the same or different from each other, n is aninteger of 0 to 3, and when n is an integer of 2 or more, R²s may be thesame or different from each other, Ar¹ and Ar² are each independently aC₆-C₆₀ aryl group, with the proviso that at least one of Ar¹ and Ar² isa pyrenyl, phenanthrenyl, or fluoranthenyl group, L¹ is selected fromthe group consisting of a single bond; a C₆-C₆₀ arylene group; adivalent C₂-C₆₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si, and P; a fluorenylenegroup; and a divalent fused ring formed by a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring wherein the arylene, heterocyclic, fluorenylene, orfused ring may be optionally substituted with one or more substituentsselected from the group consisting of deuterium, halogen, a silane groupsubstituted or unsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ arylgroup, a siloxane group, a cyano group, a nitro group, a C₁-C₂₀alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkyl group, aC₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenyl group, and L² and L³are each independently selected from the group consisting of a singlebond; and a C₆-C₆₀ arylene group, with the proviso that: i. both L² andL³ are not a single bond at the same time, ii. where L² or L³ is aC₆-C₆₀ arylene group, the arylene group is substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group substituted or unsubstituted with a C₁-C₂₀ alkyl group or aC₆-C₂₀ aryl group, a C₁-C₂₀ alkyl group, and a C₂-C₂₀ alkenyl group,iii. Ar¹ and Ar² may be each optionally substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group substituted or unsubstituted with a C₁-C₂₀ alkyl group or aC₆-C₂₀ aryl group, a C₁-C₂₀ alkyl group and a C₂-C₂₀ alkenyl group, andiv. at least one of L¹, L², Ar¹ and Ar² is substituted with at least onedeuterium.
 2. An organic electric element comprising a first electrode,a second electrode, and an organic material layer formed between thefirst electrode and the second electrode, wherein the organic materiallayer comprises the compound of claim
 1. 3. The organic electric elementof claim 2, wherein the organic material layer comprises at least onelayer of a hole injection layer, a hole transport layer, anemission-auxiliary layer and an light emitting layer.
 4. The organicelectric element of claim 2, wherein the organic material layer isformed by any one of the processes of spin coating, nozzle printing,inkjet printing, slot coating, dip coating or roll-to-roll.
 5. Anelectronic device comprising a display device and a control unit fordriving the display device, wherein the display device comprises theorganic electric element of claim
 2. 6. The electronic device of claim5, wherein the organic electric element is an organic light emittingdiode, an organic solar cell, an organic photo conductor, an organictransistor, or an element for monochromatic or white illumination.
 7. Acompound selected from the group consisting of the compounds below:


8. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises the compound of claim
 7. 9. An electronic device comprising adisplay device and a control unit for driving the display device,wherein the display device comprises the organic electric element ofclaim 8.